EP3315631B1 - Agent de traitement de surface de tôle d'acier et tôle d'acier doté d'un film de revêtement constitué de ce dernier - Google Patents

Agent de traitement de surface de tôle d'acier et tôle d'acier doté d'un film de revêtement constitué de ce dernier Download PDF

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Publication number
EP3315631B1
EP3315631B1 EP16814055.6A EP16814055A EP3315631B1 EP 3315631 B1 EP3315631 B1 EP 3315631B1 EP 16814055 A EP16814055 A EP 16814055A EP 3315631 B1 EP3315631 B1 EP 3315631B1
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EP
European Patent Office
Prior art keywords
mass
parts
steel sheet
surface treatment
treatment agent
Prior art date
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Application number
EP16814055.6A
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German (de)
English (en)
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EP3315631A4 (fr
EP3315631A1 (fr
Inventor
Ryuichi Matsuoka
Yasutaka Oka
Sadamu Nagahama
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
DIC Corp
Original Assignee
DIC Corp
Dainippon Ink and Chemicals Co Ltd
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Publication of EP3315631A4 publication Critical patent/EP3315631A4/fr
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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/40—High-molecular-weight compounds
    • C08G18/48—Polyethers
    • C08G18/4854—Polyethers containing oxyalkylene groups having four carbon atoms in the alkylene group
    • C—CHEMISTRY; METALLURGY
    • C23—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; CHEMICAL SURFACE TREATMENT; DIFFUSION TREATMENT OF METALLIC MATERIAL; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL
    • C23C—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; SURFACE TREATMENT OF METALLIC MATERIAL BY DIFFUSION INTO THE SURFACE, BY CHEMICAL CONVERSION OR SUBSTITUTION; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL
    • C23C26/00—Coating not provided for in groups C23C2/00 - C23C24/00
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/08—Processes
    • C08G18/0804—Manufacture of polymers containing ionic or ionogenic groups
    • C08G18/0819—Manufacture of polymers containing ionic or ionogenic groups containing anionic or anionogenic groups
    • C08G18/0823—Manufacture of polymers containing ionic or ionogenic groups containing anionic or anionogenic groups containing carboxylate salt groups or groups forming them
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/08—Processes
    • C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
    • C08G18/12—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step using two or more compounds having active hydrogen in the first polymerisation step
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/30—Low-molecular-weight compounds
    • C08G18/32—Polyhydroxy compounds; Polyamines; Hydroxyamines
    • C08G18/3203—Polyhydroxy compounds
    • C08G18/3215—Polyhydroxy compounds containing aromatic groups or benzoquinone groups
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/40—High-molecular-weight compounds
    • C08G18/42—Polycondensates having carboxylic or carbonic ester groups in the main chain
    • C08G18/4236—Polycondensates having carboxylic or carbonic ester groups in the main chain containing only aliphatic groups
    • C08G18/4238—Polycondensates having carboxylic or carbonic ester groups in the main chain containing only aliphatic groups derived from dicarboxylic acids and dialcohols
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/65—Low-molecular-weight compounds having active hydrogen with high-molecular-weight compounds having active hydrogen
    • C08G18/66—Compounds of groups C08G18/42, C08G18/48, or C08G18/52
    • C08G18/6666—Compounds of group C08G18/48 or C08G18/52
    • C08G18/667—Compounds of group C08G18/48 or C08G18/52 with compounds of group C08G18/32 or polyamines of C08G18/38
    • C08G18/6674—Compounds of group C08G18/48 or C08G18/52 with compounds of group C08G18/32 or polyamines of C08G18/38 with compounds of group C08G18/3203
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/72—Polyisocyanates or polyisothiocyanates
    • C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
    • C08G18/76—Polyisocyanates or polyisothiocyanates cyclic aromatic
    • C08G18/7657—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings
    • C08G18/7664—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings containing alkylene polyphenyl groups
    • C08G18/7671—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings containing alkylene polyphenyl groups containing only one alkylene bisphenyl group
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D175/00—Coating compositions based on polyureas or polyurethanes; Coating compositions based on derivatives of such polymers
    • C09D175/04—Polyurethanes
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D175/00—Coating compositions based on polyureas or polyurethanes; Coating compositions based on derivatives of such polymers
    • C09D175/04—Polyurethanes
    • C09D175/06—Polyurethanes from polyesters
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D175/00—Coating compositions based on polyureas or polyurethanes; Coating compositions based on derivatives of such polymers
    • C09D175/04—Polyurethanes
    • C09D175/08—Polyurethanes from polyethers
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
    • C09D5/02—Emulsion paints including aerosols
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
    • C09D5/08—Anti-corrosive paints

Definitions

  • the present invention relates to a steel sheet surface treatment agent which is used for the surface of various types of metal substrates, such as a zinc-plated steel sheet and an aluminum-zinc alloy steel sheet, and a steel sheet having a coating film of the steel sheet surface treatment agent.
  • a steel sheet surface treatment agent is generally required to form a coating film which can prevent a metal substrate surface from deteriorating.
  • the industrial fields demand a steel sheet surface treatment agent to form a coating film having not only a warm water resistance and a solvent resistance but also a chemical resistance at such a level that the film can prevent the substrate from deteriorating due to the deposition of a chemical, such as a cleaning agent, acid rain, or the like.
  • the steel sheet surface treatment agent having the above-mentioned properties is often required especially in the application of surface protection for a metal substrate which is not rust resistant.
  • an aqueous resin composition for a metal surface treatment agent which contains an aqueous vinyl-modified epoxy ester resin and a carboxyl group-containing aqueous urethane resin, where the carboxyl group-containing aqueous urethane resin is a polyester urethane resin obtained by reacting a polyester polyol prepared from an acid component and a glycol component without carboxyl group; a polyisocyanate compound; and a chain extender that contains a glycol component with a carboxyl group (see, for example, PTL 1).
  • a coating film formed from the above-mentioned aqueous resin composition for metal surface treatment agent can not satisfactorily prevent deterioration of a metal substrate for a long term in respect of the chemical resistance and corrosion resistance.
  • the coating film cannot satisfactorily prevent a metal substrate rust from a practical point of view in some cases.
  • US 2012/016075 A1 describes a polyurethane dispersion and a method for producing the same.
  • US 5,817,733 A describes polyurethane resins, processes for their preparation, and their use in water-dilutable coating compositions.
  • US 6,649,688 A describes a coating composition comprising at least three components, including a component comprising at least one polyisocyanate dispersed or dissolved in one or more organic, optionally water dilutable solvents, it preparation and use.
  • WO 2014/204248 A1 relates to a method of manufacturing a planarizing film having good functionality in terms of planarizing performance while having a thickness of about 10 ⁇ m or less by drawing a material having planarizing functionality such as a PVA-based resin, while preventing tearing or curling during a drawing process.
  • EP 2 868 626 A1 describes polyurethane elastomer nanocomposites and a method of their manufacturing.
  • US 2002/111424 A1 describes a method for preparing a water-based urethane resin composition.
  • US 2003/083428 A1 describes a polymer dispersions suitable for reactive systems.
  • EP 2 877 508 A1 describes aqueously dispersible polyurethanes.
  • WO 2015/019899 A1 describes an aqueous resin composition, a laminate produced using same, and an image display device.
  • An object of the present invention is to provide a steel sheet surface treatment agent which forms a coating film having excellent heat yellowing resistance, chemical resistance, corrosion resistance, and a capability of preventing deterioration of various types of metal substrates.
  • the present inventors conducted extensive and intensive studies with a view toward solving the above-mentioned problems, and found that a steel sheet surface treatment agent containing an aqueous urethane resin, which is obtained by reacting a urethane prepolymer containing an aromatic polyisocyanate and a specific alcohol solvent as a terminator, forms a coating film that exhibits an excellent heat yellowing resistance, a chemical resistance, and a corrosion resistance and a capability of preventing deterioration of a metal substrate, thereby completing the present invention.
  • the present invention is directed to a steel sheet surface treatment agent containing an aqueous urethane resin composition obtained by dispersing in (C) an aqueous medium a urethane resin obtained by reacting (A) a urethane prepolymer having an isocyanate group and (B) a terminator containing (b1) an alcohol solvent, wherein the urethane prepolymer (A) is obtained by reacting (a1) a polyol and (a2) a polyisocyanate containing an aromatic polyisocyanate, wherein the polyol (a1) includes a polyether polyol, wherein the alcohol solvent (b1) includes hexanol, heptanol, octanol, nonanol, undecanol, 1,2-propanediol, 1,3-propanediol, 1,2-butanediol, 1,3-butanediol, 1,4-butanediol, 2,3-
  • the steel sheet surface treatment agent of the present invention forms a coating film having very excellent heat yellowing resistance, chemical resistance, and corrosion resistance, and therefore can be used in the application of surface protection for various types of metal substrates.
  • the examples of metal substrates for the application of the steel sheet surface treatment agent of the present invention include plated steel sheets such as a zinc-plated steel sheet and an aluminum-zinc alloy steel sheet; an aluminum sheet; an aluminum alloy sheet; an electrical steel sheet; a copper sheet; and a stainless steel sheet.
  • the steel sheet surface treatment agent of the present invention forms a coating film with excellent corrosion resistance and prevents these metal substrates from rusting, and therefore the agent is advantageously used in various types of members such as building materials including an outer wall and roofing; civil engineering materials including a guardrail, a sound barrier and a drainage conduit; household appliances; industrial machines; and exterior automotive trims.
  • the steel sheet surface treatment agent of the present invention contains an aqueous urethane resin composition which is obtained by dispersing in (C) an aqueous medium a urethane resin obtained by reacting (A) a urethane prepolymer having an isocyanate group and (B) a terminator containing (b1) an alcohol solvent, wherein the urethane prepolymer (A) is obtained by reacting (a1) a polyol and (a2) a polyisocyanate containing an aromatic polyisocyanate, wherein the polyol (a1) includes a polyether polyol, wherein the alcohol solvent (b1) includes hexanol, heptanol, octanol, nonanol, undecanol, 1,2-propanediol, 1,3-propanediol, 1,2-butanediol, 1,3-butanediol, 1,4-butanediol, 2,3-butaned
  • urethane prepolymer (A) a urethane prepolymer having an isocyanate group is used which is obtained by reacting a polyol (a1) and a polyisocyanate (a2) containing an aromatic polyisocyanate.
  • the polyol (a1) includes a polyether polyol and may further include a polyester polyol, a polycarbonate polyol, and a polyolefin polyol.
  • a polyether polyol is used from the viewpoint of the ability to form a coating film with excellent alkali resistance.
  • These polyols (a1) may be used individually or in combination.
  • polyether polyol as the polyol (a1) examples include those obtained by subjecting alkylene oxide to addition polymerization using as an initiator one type or two or more types of compounds having two or more active hydrogen atoms.
  • the initiator examples include ethylene glycol, diethylene glycol, triethylene glycol, trimethylene glycol, 1,2-propanediol, 1,3-propanediol, 1,3-butanediol, 1,4-butanediol, 1,6-hexanediol, neopentyl glycol, glycerol, trimethylolethane, trimethylolpropane, sorbitol, sucrose, aconitic acid, trimellitic acid, hemimellitic acid, phosphoric acid, ethylenediamine, diethylenetriamine, triisopropanolamine, pyrogallol, dihydroxybenzoic acid, hydroxyphthalic acid, and 1,2,3-propanetrithiol.
  • alkylene oxide examples include ethylene oxide, propylene oxide, butylene oxide, styrene oxide, epichlorohydrin, and tetrahydrofuran.
  • polyoxytetramethylene glycol formed by subjecting tetrahydrofuran to ring-opening is preferably used.
  • a polyether polyol having a number average molecular weight of 500 to 3,000 is preferably used from the viewpoint of achieving a further improvement of the adhesion to a substrate.
  • polyester polyol examples include those obtained by subjecting a low molecular-weight polyol and a polycarboxylic acid to esterification reaction; a polyester obtained by subjecting a cyclic ester compound such as ⁇ -caprolactone to ring-opening polymerization reaction; and copolymerized polyesters thereof.
  • low molecular-weight polyol examples include polyols having a molecular weight of about 50 to 300 such as aliphatic polyols including ethylene glycol, propylene glycol, 1,4-butanediol, 1,6-hexanediol, diethylene glycol, neopentyl glycol, and 1,3-butanediol; alicyclic structure-containing polyols, such as cyclohexanedimethanol; and aromatic structure-containing polyols, such as bisphenol compounds, e.g., bisphenol A and bisphenol F, and alkylene oxide addition products thereof.
  • aliphatic polyols including ethylene glycol, propylene glycol, 1,4-butanediol, 1,6-hexanediol, diethylene glycol, neopentyl glycol, and 1,3-butanediol
  • alicyclic structure-containing polyols such as cyclohex
  • polycarboxylic acid for the polyester polyol production examples include aliphatic polycarboxylic acids such as succinic acid, adipic acid, sebacic acid and dodecanedicarboxylic acid; aromatic polycarboxylic acids such as terephthalic acid, isophthalic acid, phthalic acid and naphthalenedicarboxylic acid; and anhydrides or ester-forming derivatives thereof.
  • polyester polyol With respect to the polyester polyol, from the viewpoint of achieving a further improvement of the adhesion to a substrate, a polyester polyol having a number average molecular weight of 500 to 3,000 is preferably used.
  • polycarbonate polyol examples include those obtained by reacting a carbonate and a polyol, and those obtained by reacting phosgene and bisphenol A or the like.
  • Examples of the carbonate include methyl carbonate, dimethyl carbonate, ethyl carbonate, diethyl carbonate, cyclo carbonate, and diphenyl carbonate.
  • a relatively low molecular-weight diol having a molecular weight of 50 to 2,000, such as ethylene glycol, diethylene glycol, 1,2-propylene glycol, dipropylene glycol, 1,4-butanediol, 1,5-pentanediol
  • a polycarbonate polyol having a number average molecular weight of 500 to 3,000 is preferably used from the viewpoint of achieving a further improvement of the adhesion to a substrate.
  • polystyrene polyol examples include polyethylene polyol, polypropylene polyol, polyisobutene polyol, hydrogenated polybutadiene polyol, and hydrogenated polyisoprene polyol.
  • the above-mentioned polyol and other polyol having a hydrophilic group can be used in combination.
  • a polyol having an anionic group, a polyol having a cationic group, or a polyol having a nonionic group can be used as a polyol other than the above-mentioned polyol (a1).
  • a polyol having an anionic group or a polyol having a cationic group is preferably used, and a polyol having an anionic group is more preferably used.
  • polyol having an anionic group examples include polyols having a carboxyl group, and polyols having a sulfonic group.
  • polystyrene resin examples include 2,2-dimethylolpropionic acid, 2,2-dimethylolbutanoic acid, 2,2-dimethylolbutyric acid, and 2,2-dimethylolvaleric acid. Of these, 2,2-dimethylolpropionic acid is preferred. Further, a polyester polyol having a carboxyl group can be used, which is obtained by reacting the polyol having a carboxyl group and various polycarboxylic acids with each other.
  • polyester polyols which are obtained by reacting a dicarboxylic acid, such as 5-sulfoisophthalic acid, sulfoterephthalic acid, 4-sulfophthalic acid, or 5-(4-sulfophenoxy)isophthalic acid, or a salt thereof and the low molecular-weight polyol mentioned above as examples of those usable in producing the polyester polyol having an aromatic structure with each other.
  • a dicarboxylic acid such as 5-sulfoisophthalic acid, sulfoterephthalic acid, 4-sulfophthalic acid, or 5-(4-sulfophenoxy)isophthalic acid, or a salt thereof
  • the low molecular-weight polyol mentioned above as examples of those usable in producing the polyester polyol having an aromatic structure with each other.
  • the polyol having a carboxyl group or the polyol having a sulfonic group is preferably used in such an amount that the acid value of the urethane resin (A) becomes 5 to 70, more preferably used in such an amount that the acid value of the urethane resin (A) becomes 10 to 50.
  • the acid value in the present invention is a theoretical value calculated based on the amount of the acid group-containing compound used, such as the polyol having a carboxyl group used in producing the urethane resin (A).
  • part of or all of the anionic group is neutralized by a basic compound or the like from the viewpoint of exhibiting excellent water dispersibility.
  • Examples of the basic compound usable in neutralizing the anionic group include organic amines having a boiling point of 200°C or higher, such as ammonia, triethylamine, morpholine, monoethanolamine, and diethylethanolamine; and metal hydroxides, such as sodium hydroxide, potassium hydroxide, and lithium hydroxide.
  • the basic compound is preferably used in such an amount that the basic group/anionic group (molar ratio) of the basic compound becomes 0.5 to 3.0, more preferably used in such an amount that the basic group/anionic group (molar ratio) becomes 0.8 to 2.0.
  • polyol having a cationic group examples include polyols having a tertiary amino group. Specific examples thereof include N-methyl-diethanolamine, and a polyol obtained by reacting a compound having two epoxys per molecule and a secondary amine with each other.
  • part of or all of the cationic group is neutralized by an acid compound, such as formic acid, acetic acid, propionic acid, succinic acid, glutaric acid, tartaric acid, or adipic acid.
  • an acid compound such as formic acid, acetic acid, propionic acid, succinic acid, glutaric acid, tartaric acid, or adipic acid.
  • the quaternizing agents include dimethyl sulfate, diethyl sulfate, methyl chloride, and ethyl chloride. Of these, dimethyl sulfate is preferably used.
  • polyol having a nonionic group examples include polyols having a polyoxyethylene structure.
  • the polyol having a hydrophilic group is preferably used in an amount in the range of from 0.3 to 10% by mass, based on the total mass of the polyol (a1) used in producing the urethane resin (A).
  • the other polyol in addition to the above-mentioned polyol, the other polyol can be used, if necessary.
  • Examples of the other polyol include relatively low molecular-weight polyols, such as ethylene glycol, diethylene glycol, 1,2-propylene glycol, dipropylene glycol, neopentyl glycol, 1,4-butanediol, 1,5-pentanediol, 3-methyl-1,5-pentanediol, 1,4-cyclohexanediol, 1,6-hexanediol, and cyclohexanedimethanol.
  • relatively low molecular-weight polyols such as ethylene glycol, diethylene glycol, 1,2-propylene glycol, dipropylene glycol, neopentyl glycol, 1,4-butanediol, 1,5-pentanediol, 3-methyl-1,5-pentanediol, 1,4-cyclohexanediol, 1,6-hexanediol, and cyclohexaned
  • an aromatic polyisocyanate is an essential component, and, if necessary, the other polyisocyanate can be used in combination with the aromatic polyisocyanate.
  • aromatic polyisocyanate examples include 1,3- or 1,4-phenylene diisocyanate, 1-methyl-2,4-phenylene diisocyanate, 1-methyl-2,6-phenylene diisocyanate, 1-methyl-2,5-phenylene diisocyanate, 1-methyl-2,6-phenylene diisocyanate, 1-methyl-3,5-phenylene diisocyanate, 1-ethyl-2,4-phenylene diisocyanate, 1-isopropyl-2,4-phenylene diisocyanate, 1,3-dimethyl-2,4-phenylene diisocyanate, 1,3-dimethyl-4,6-phenylene diisocyanate, 1,4-dimethyl-2,5-phenylene diisocyanate, diethylbenzene diisocyanate, diisopropylbenzene diisocyanate, 1-methyl-3,5-diethylbenzene diisocyanate, 3-methyl-1,5-diethylbenzene
  • At least one polyisocyanate selected from the group consisting of toluene diisocyanate, diphenylmethane diisocyanate, and xylylene diisocyanate is preferably used.
  • aromatic polyisocyanates can be used individually or in combination.
  • Examples of the other polyisocyanate include aliphatic polyisocyanates, such as tetramethylene diisocyanate, 1,6-hexamethylene diisocyanate, dodecamethylene diisocyanate, and trimethylhexamethylene diisocyanate; and alicyclic polyisocyanates, such as 1,3-cyclopentylene diisocyanate, 1,3-cyclohexylene diisocyanate, 1,4-cyclohexylene diisocyanate, 1,3-bis(isocyanatomethyl)cyclohexane, 1,4-bis(isocyanatomethyl)cyclohexane, lysine diisocyanate, isophorone diisocyanate, 4,4'-dicyclohexylmethane diisocyanate, 2,4'-dicyclohexylmethane diisocyanate, 2,2'-dicyclohexylmethane diisocyanate, and 3,3'-dimethyl-4
  • the urethane prepolymer (A) having an isocyanate group can be produced by mixing together and reacting the polyol (a1) and the polyisocyanate (a2) with each other, for example, in the absence of a solvent or in the presence of an organic solvent.
  • the reaction of the polyol (a1) and the polyisocyanate (a2) is preferably conducted so that, for example, the equivalent ratio of the isocyanate group of the polyisocyanate (a2) to the hydroxyl group of the polyol (a1) [isocyanate group/hydroxyl group] becomes in the range of from 0.9 to 3, more preferably in the range of from 0.95 to 2.
  • the reaction of the polyol (a1) and the polyisocyanate (a2) is generally conducted at a temperature in the range of from 50 to 150°C.
  • the isocyanate group equivalent of the urethane prepolymer (A) obtained by the above-mentioned reaction is preferably 3,500 to 100,000 g/eq., more preferably 10,000 to 60,000 g/eq. from the viewpoint of the ability to form a coating film having excellent corrosion resistance.
  • organic solvent usable in producing the urethane prepolymer (A) examples include ketone solvents, such as acetone and methyl ethyl ketone; ether solvents, such as tetrahydrofuran and dioxane; acetate solvents, such as ethyl acetate and butyl acetate; nitrile solvents, such as acetonitrile; and amide solvents, such as dimethylformamide and N-methylpyrrolidone. These organic solvents can be used individually or in combination.
  • ketone solvents such as acetone and methyl ethyl ketone
  • ether solvents such as tetrahydrofuran and dioxane
  • acetate solvents such as ethyl acetate and butyl acetate
  • nitrile solvents such as acetonitrile
  • amide solvents such as dimethylformamide and N-methylpyrrolidone.
  • part of or all of the organic solvent may be removed by, for example, distilling off under a reduced pressure.
  • the alcohol solvent (b1) having a boiling point in the range of from 150 to 350°C and having a number average molecular weight of 500 or less is essential, and, if necessary, the other terminator can be used in combination with the alcohol solvent.
  • the alcohol component volatilizes, so that the reaction of the alcohol with the polyisocyanate (a2) is unsatisfactory.
  • the polyisocyanate (a2) remains unreacted, and the remaining polyisocyanate (a2) and water are reacted with each other to form an aromatic amine.
  • the formed aromatic amine tends to cause yellowing, and, the aromatic amine likely causes the coating film to be yellowed when a coating film is formed from the resultant surface treatment agent, leading to a problem of the appearance.
  • the alcohol solvent does not volatilize during the solvent removal and/or drying of a coating film, and the alcohol solvent remains in the formed coating film when a coating film is formed from the resultant surface treatment agent.
  • the coating film is plasticized, so that the corrosion resistance of the coating film becomes unsatisfactory.
  • the alcohol solvent (b1) includes hexanol, heptanol, octanol, nonanol, undecanol, 1,2-propanediol, 1,3-propanediol, 1,2-butanediol, 1,3-butanediol, 1,4-butanediol, 2,3-butanediol, 1,2-pentanediol, 1,5-pentanediol, 1,2-hexanediol, or 1,6-hexanediol.
  • At least one alcohol solvent selected from the group consisting of 1,2-propanediol, 1,2-butanediol, and 1,3-butanediol is preferred.
  • the amount of the alcohol solvent (b1) contained is in the range of from 0.1 to 10 parts by mass relative to 100 parts by mass of the urethane prepolymer (A).
  • the reaction of the alcohol with the polyisocyanate (a2) is unsatisfactory.
  • the polyisocyanate (a2) remains unreacted, and the remaining polyisocyanate (a2) and water are reacted with each other to form an aromatic amine.
  • the formed aromatic amine tends to cause yellowing, and, when a coating film is formed from the resultant surface treatment agent, the aromatic amine presumably causes the coating film to be yellowed, thereby raising a problem of the appearance.
  • the amount of the alcohol solvent (b1) contained is more than 20 parts by mass relative to 100 parts by mass of the urethane prepolymer (A)
  • the alcohol solvent does not volatilize during the solvent removal and/or drying of a coating film, and the alcohol solvent remains in the formed coating film when a coating film is formed from the resultant surface treatment agent.
  • the coating film is plasticized, so that the corrosion resistance of the coating film becomes unsatisfactory.
  • Examples of the other terminator include dibutylamine, ethanolamine, diethanolamine, aminosilane, and ammonia.
  • the urethane prepolymer (A) and the terminator (B) are reacted with each other, so that a urethane resin can be obtained.
  • Examples of the aqueous medium (C) used in the steel sheet surface treatment agent of the present invention include waster, an organic solvent miscible with water, and a mixture thereof.
  • Examples of the organic solvent miscible with water include alcohol solvents, such as methanol, ethanol, n-propanol, and isopropanol; ketone solvents, such as acetone and methyl ethyl ketone; polyalkylene glycols, such as ethylene glycol, diethylene glycol, and propylene glycol; alkyl ether solvents, such as polyalkylene glycol; and lactam solvents, such as N-methyl-2-pyrrolidone.
  • These organic solvents miscible with water can be used individually or in combination.
  • aqueous medium (C) taking into consideration the safety and reduction of the burden on the environment, only water, or a mixture of water and an organic solvent miscible with water is preferred, and only water is more preferred.
  • the aqueous urethane resin composition used in the steel sheet surface treatment agent of the present invention can be produced by, specifically, a method having:
  • the isocyanate group of the urethane prepolymer (A) is completely reacted by the terminator (B) from the viewpoint of achieving an improvement of the heat yellowing resistance of the resultant coating film.
  • the reaction of the urethane prepolymer (A) and the terminator (B) is conducted at 55 to 150°C, and, for causing the terminator (B) to completely react the isocyanate group of the urethane prepolymer (A), the reaction is conducted preferably at 60 to 150°C, more preferably at 70 to 150°C.
  • the steel sheet surface treatment agent of the present invention can be used in coating of various types of metal substrates for the purpose of surface protection of various types of metal substrates and imparting design properties to various types of metal substrates.
  • the metal substrate examples include plated steel sheets, such as a zinc-plated steel sheet and an aluminum-zinc alloy steel sheet, an aluminum sheet, an aluminum alloy sheet, an electrical steel sheet, a copper sheet, and a stainless steel sheet.
  • plated steel sheets such as a zinc-plated steel sheet and an aluminum-zinc alloy steel sheet, an aluminum sheet, an aluminum alloy sheet, an electrical steel sheet, a copper sheet, and a stainless steel sheet.
  • the steel sheet surface treatment agent of the present invention is advantageous in that even when the crosslinked coating film of the agent has a thickness as small as about 5 ⁇ m, a coating film having excellent chemical resistance including an acid resistance, an alkali resistance and the like can be formed. Further, the steel sheet surface treatment agent is advantageous in that even when the crosslinked coating film of the agent has a thickness as small as about 1 ⁇ m, a coating film having excellent chemical resistance including an acid resistance, an alkali resistance and the like can be formed.
  • the steel sheet surface treatment agent of the present invention is applied to a substrate, and dried and cured, forming a coating film.
  • Examples of the method for application include a spraying method, a curtain coater method, a flow coater method, a roll coater method, a brushing method, and an immersion method.
  • the drying may be natural drying made at room temperature, but drying by heating can be made.
  • the drying by heating is preferably conducted generally at 40 to 250°C for a period of time of about 1 to 600 seconds.
  • plated steel sheets such as a zinc-plated steel sheet and an aluminum-zinc alloy steel sheet, an aluminum sheet, an aluminum alloy sheet, an electrical steel sheet, a copper sheet, and a stainless steel sheet, which are used in the applications of automobiles, household appliances, building materials, and the like.
  • the obtained organic solvent solution of the urethane prepolymer was cooled to 40°C, and 35 parts by mass of triethylamine was added to the solution to neutralize part of or all of the carboxyl group of the urethane prepolymer, and 2,699 parts by mass of water was further added and the resultant mixture was satisfactorily stirred to obtain an aqueous dispersion of a urethane resin.
  • 2 parts by mass of ethylenediamine was added to the aqueous dispersion to cause chain extension, and the resultant mixture was subjected to aging and solvent removal to obtain a steel sheet surface treatment agent (C4) having a nonvolatile content of 30% by mass.
  • a polypropylene film having an outer frame having a height of 1 mm was put on an A4-size glass plate, and the steel sheet surface treatment agent obtained with respect to each of Examples 1 to 10 and Comparative Examples 1 to 4 was applied onto the polypropylene film in an amount of 6 g/100 cm 2 , and dried at 25°C for one day to form a coating film having a thickness of about 150 ⁇ m.
  • the formed coating film was subjected to heating treatment at 108°C for 2 hours, and then released from the polypropylene film, and the resultant coating film was used as a test film.
  • the obtained test film was subjected to heat discoloration resistance test in which the film was allowed to stand at a temperature of 200°C for 30 minutes.
  • a b value which indicates yellowness was measured using spectrocolorimeter "CM-3500d", manufactured by Konica Minolta Holdings, Inc., and a difference ⁇ b between the b values before and after the test was determined, and evaluated in accordance with the following criteria.
  • the steel sheet surface treatment agent obtained with respect to each of Examples 1 to 13 and Comparative Examples 1 to 4 was applied onto a 55% by mass aluminum-zinc alloy-plated steel sheet which is not subjected to surface treatment so as to provide a thickness of 1 ⁇ m, and dried at 250°C for 10 seconds to prepare a test specimen.
  • the surface of the coating film constituting the test specimen was scratched by a cutting knife at such a depth that the knife reached the substrate, and subjected to salt spray test using a salt spray tester, manufactured by Suga Test Instruments Co., Ltd., and, after 240 hours, the rusting area was visually determined and evaluated.
  • the measurement was made by a method in accordance with the JIS test method (JIS Z2371:2000).
  • Comparative Example 1 is an example in which an alicyclic polyisocyanate was used as a polyisocyanate component which is a raw material for a urethane prepolymer. It has been confirmed that the coating film obtained using the steel sheet surface treatment agent in Comparative Example 1 is excellent in the heat yellowing resistance, but is not satisfactory at all in the chemical resistance and corrosion resistance.
  • Comparative Example 2 is an example in which methanol having the boiling point which is outside of the range defined in the present invention (boiling point: 65.4°C) was used as a terminator. It has been confirmed that the coating film obtained using the steel sheet surface treatment agent in Comparative Example 2 is not satisfactory at all in the heat yellowing resistance and corrosion resistance, and further is not satisfactory in the chemical resistance.
  • Comparative Example 3 is an example in which polypropylene glycol having the number average molecular weight which is outside of the range defined in the present invention (number average molecular weight: 650) was used as a terminator. It has been confirmed that the coating film obtained using the steel sheet surface treatment agent in Comparative Example 3 is not satisfactory at all in the heat yellowing resistance, chemical resistance, and corrosion resistance.
  • Comparative Example 4 is an example in which no terminator was used. It has been confirmed that the coating film obtained using the steel sheet surface treatment agent in Comparative Example 4 is excellent in the chemical resistance (alkali resistance), but is not satisfactory at all in the heat yellowing resistance.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Health & Medical Sciences (AREA)
  • Materials Engineering (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Manufacturing & Machinery (AREA)
  • Mechanical Engineering (AREA)
  • Metallurgy (AREA)
  • Dispersion Chemistry (AREA)
  • Polyurethanes Or Polyureas (AREA)
  • Paints Or Removers (AREA)
  • Other Surface Treatments For Metallic Materials (AREA)
  • Laminated Bodies (AREA)

Claims (6)

  1. Agent de traitement de surface pour tôles d'acier, comprenant une composition aqueuse de résine uréthane obtenue par dispersion dans (C) un milieu aqueux d'une résine uréthane obtenue par réaction (A) d'un prépolymère uréthane ayant un groupe isocyanate et (B) d'un terminateur contenant (b1) un solvant alcoolique,
    dans lequel le prépolymère uréthane (A) est obtenu par réaction (a1) d'un polyol et (a2) d'un polyisocyanate contenant un polyisocyanate aromatique,
    dans lequel le polyol (a1) comprend un polyol de polyéther,
    dans lequel le solvant alcool (b1) comprend l'hexanol, l'heptanol, l'octanol, le nonanol, l'undécanol, le 1,2-propanediol, le 1,3-propanediol, le 1,2-butanediol, le 1,3-butanediol, le 1,4-butanediol, le 2,3-butanediol, le 1,2-pentanediol, le 1,5-pentanediol, le 1,2-hexanediol, ou le 1,6-hexanediol,
    dans lequel le point d'ébullition du solvant alcoolique (b1) est compris entre 150 et 350 C°,
    dans lequel le poids moléculaire moyen en nombre du solvant alcoolique (b1) est inférieur ou égal à 500, et
    dans lequel la teneur en solvant alcoolique (b1) est comprise entre 0,1 et 10 parties en masse par rapport à 100 parties en masse du prépolymère uréthane (A).
  2. Agent de traitement de surface des tôles d'acier selon la revendication 1, dans lequel le solvant alcoolique (b1) est au moins un solvant alcoolique choisi dans le groupe constitué par le 1,2-propanediol, le 1,2-butanediol et le 1,3-butanediol.
  3. Agent de traitement de surface des tôles d'acier selon la revendication 1, dans lequel le polyisocyanate aromatique est au moins un polyisocyanate choisi dans le groupe constitué par le diisocyanate de toluène, le diisocyanate de diphénylméthane et le diisocyanate de xylylène.
  4. Agent de traitement de surface des tôles d'acier selon la revendication 1, dans lequel l'équivalent en groupe isocyanate du prépolymère uréthane (A) est de 3 500 g/éq. ou plus.
  5. Tôle d'acier comprenant un film de revêtement de l'agent de traitement de surface de tôle d'acier selon l'une des revendications 1 à 4.
  6. Méthode de production d'une composition aqueuse de résine d'uréthane, comprenant :
    la première étape de faire réagir un polyol (a1) et un polyisocyanate (a2) contenant un polyisocyanate aromatique pour obtenir un prépolymère uréthane (A) ayant un groupe isocyanate ;
    la deuxième étape de faire réagir le prépolymère uréthane (A) obtenu et un terminateur (B) contenant un solvant alcoolique (b1) à 55° C ou plus, et de disperser la résine uréthane obtenue dans un milieu aqueux (C) pour obtenir une dispersion aqueuse de la résine uréthane ; et
    la troisième étape de soumettre la dispersion aqueuse de la résine uréthane au vieillissement et/ou à l'élimination du solvant,
    dans laquelle le polyol (a1) comprend un polyol de polyéther,
    dans laquelle le solvant alcoolique (b1) est au moins l'un des suivants : hexanol, heptanol, octanol, nonanol, undécanol, 1,2-propanediol, 1,3-propanediol, 1,2-butanediol, 1,3-butanediol, 1,4-butanediol, 2,3-butanediol, 1,2-pentanediol, 1,5-pentanediol, 1,2-hexanediol, et 1,6-hexanediol,
    dans laquelle le solvant alcoolique (b1) présente un point d'ébullition compris entre 150 et 350 °C,
    dans laquelle le poids moléculaire moyen en nombre du solvant alcoolique (b1) est inférieur ou égal à 500, et
    dans laquelle la teneur en solvant alcoolique (b1) est comprise entre 0,1 et 10 parties en masse par rapport à 100 parties en masse du prépolymère uréthane (A).
EP16814055.6A 2015-06-26 2016-05-10 Agent de traitement de surface de tôle d'acier et tôle d'acier doté d'un film de revêtement constitué de ce dernier Active EP3315631B1 (fr)

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PCT/JP2016/063840 WO2016208284A1 (fr) 2015-06-26 2016-05-10 Agent de traitement de surface de tôle d'acier et tôle d'acier doté d'un film de revêtement constitué de ce dernier

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EP3333209B1 (fr) * 2016-12-07 2023-09-20 Henkel AG & Co. KGaA Matrice de résine de polyuréthane thermoplastique
JP2020001325A (ja) * 2018-06-29 2020-01-09 日鉄日新製鋼株式会社 有機樹脂で被覆された金属素形材およびその製造方法
WO2020167757A1 (fr) * 2019-02-15 2020-08-20 Avery Dennison Corporation Synthèse de polyuréthane
CN113980228A (zh) * 2021-10-12 2022-01-28 广州先进技术研究所 一种大分子表面改性剂及其合成方法
CN114453226A (zh) * 2021-12-30 2022-05-10 安徽志诚机电零部件有限公司 一种聚氨酯防腐耐磨热熔铝箔复合制备方法

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JPH0822900B2 (ja) * 1984-07-30 1996-03-06 大日本インキ化学工業株式会社 水性ポリエステルウレタン樹脂組成物
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EP3315631A4 (fr) 2019-03-13
EP3315631A1 (fr) 2018-05-02
TWI713538B (zh) 2020-12-21
CN107709615B (zh) 2019-10-11
TW201710419A (zh) 2017-03-16
JPWO2016208284A1 (ja) 2018-02-15
WO2016208284A1 (fr) 2016-12-29
CN107709615A (zh) 2018-02-16

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